Hydrochloric Acid → 1-[4-(Hydroxymethyl)phenyl]-2-cyanoindole

HRID 1769201Notes

Reaction equation

HRID 1769201 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]#[N:20])=[CH:6][CH:5]=1)(O)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].Cl>O1CCCC1.O1CCCC1.O>[OH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]#[N:20])=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 104004611-(4-Carboxyphenyl)-2-cyanoindole

Product 1

HCID 103546391-[4-(Hydroxymethyl)phenyl]-2-cyanoindoleYield 56.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2.8 g (0.0107 mol) of 1-(4-carboxyphenyl)-2-cyanoindole was dissolved in 100 ml tetrahydrofuran and cooled in an ice-bath. 1.5 ml (0.01 mol) of triethylamine was added, followed by the dropwise addition of 1.1 ml (0.01 mol) ethyl chloroformate. After stirring for 20 minutes the precipitate was removed by filtration and a solution of 1.2 g (0.1 mol) sodium borohydride in 60 ml tetrahydrofuran-water 3:1 was added dropwise to the filtrate. After stirring an additional 20 minutes, 5 ml of 10% hydrochloric acid was added, and the mixture extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated to an oil. The oily material was chromatographed on silica gel, eluting with ethyl acetate-hexane 7:3 to give 1.5 g (0.006 mole) of 1-[4-(hydroxymethyl)phenyl]-2-cyanoindole as an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. customwas removed by filtration
  3. stirringAfter stirring an additional 20 minutes
  4. extractionthe mixture extracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated to an oil
  7. customThe oily material was chromatographed on silica gel
  8. washeluting with ethyl acetate-hexane 7:3

Sources & evidence

ORD record
ord-4d1be5bfb4f9499baf49b0807332aa50
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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